


Try This On For Size

by Saesama



Category: Homestuck
Genre: Aftercare, Boundaries, Crossdressing, Dom!Jane, Dom/sub, F/M, Pegging, Subspace, hinted OT8
Language: English
Status: Completed
Published: 2014-08-19
Updated: 2014-08-19
Packaged: 2018-02-13 19:51:40
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,220
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2163057
Author URL: https://archiveofourown.org/users/Saesama/pseuds/Saesama
Summary: <blockquote class="userstuff">
              <p>You're the only proper Dom you know. He's the most magnificent sub you've ever seen.</p><p>He's a gay man. You're... well, not.</p><p>You both find ways to make it work.</p>
            </blockquote>





	Try This On For Size

You asked the others, and they agree; Dirk always takes a day to get used to people. It's like he needs a night to recalibrate his space to include another person, even if, say, Jake left his place the day before you arrived.

So, no real contact the first night, not even hugs or cuddles. You're used to it by now, and you're not offended when he opens his front door and greets you with the most stoic of head-nods.

You poke him in the gut to watch the air poof out of his lungs and the smile try and break his scowl.

"Dork," you say, low and fond, as you pass him into his apartment. "How have you been?"

Dirk shrugs and shuts the door. "You know me," he says. "All of the irons in all of the fires." You feel him poke the garment bags slung over your shoulder. "Going to a ball?"

You grin at him and stride down the hall to his room. "A gift for you, actually."

"I'm flattered. What is it?"

One bag gets hung up in his closet and you shoulder the other again. "A surprise," you say firmly. "No peeking until I say."

Dirk cocks a brow at you. "Cold, Crocker. Leaving a tease for me in my own space. How will I resist?"

You level a hard look at Dirk. "No peeking," you repeat, with just a bit of a hard edge in your voice. You can see the faint tremor in his shoulders at the tone and you feel a little bad for doing this to him before he finishes calibrating to your presence, but you and he will both get over it. You deliberately relax your pose and tone before you speak again. "Do you actually have food in your fridge, or am I going to have to go grocery shopping?" _I'm sorry._

He snorts and waves in the general direction of the kitchen. "I went shopping myself," he says. "I bought veggies like a real grown up and everything." _Apology accepted._

"Oh, good." The other bag and your suitcase go in the tiny spare bedroom. "Let's use them tomorrow and order pizza tonight."

"Woman after my own heart, Crocker."

o o o

The tech convention you're in town for gives you two weeks with Dirk and the first two days he spends reverse-engineering the CrockerCorp prototypes you brought with you. Night one is in the guest room, alone. Night two, Dirk's unwound enough and you abandon the way-too-small guest bed in favor of his.

Morning four, you wake up to a heavy case of morning wood against your butt and you smile. Dirk's general lack of interest in boobs or hoo-hah means the rare sex between you gets creative, but you've found ways that work. You grind back against him and he makes snuffly noises into your hair. "Morning, starshine," you hum. He grunts and rocks his hips into yours.

A bit of sleepy shuffling gets both pairs of underwear down around your knees and he slides his erection between your thighs, high up where the head of his dick bumps your clit on the upswing. It's slow and lazy and good, a sloppy Saturday morning orgasm that makes a mess of your thighs, and Dirk doesn't make any kind of articulate noise until he groans your name into your hair. You roll over and kiss him and here, Dirk, have some of your mess back, you're welcome. "Gross," he mutters against your mouth.

"It's your cooties, not my icky girl ones," you counter.

"It's a gift you've thrown back in my lap." He sits up and stretches, long and lean. "I picked that out just for you, and look what you did. You come in my house, on the day my daughter is to be married-"

"Now who's gross?" You poke him in the ribs, aborting his stretch, and roll out of bed. "Clean up, Dirk," you say, that hard edge back in your voice. Today is a good day for your surprise. "We're going out."

Dirk immediately gets very quiet. His shoulders drop and he looks at his hands in his lap. "Yes, Jane," he says quietly.

"Yes, _sir_ ," you correct, icy cold.

Dirk shudders and stands. "Yes, sir."

o o o

Your group is a varied mix of kinks and fetishes, but you're the only one who honest-to-Betsy qualifies as a Dominate. John's close, but he's more 'pushy brat' than an actual Dom, and you despair of him ever really getting over it. Oh well. You're not going to worry about John when you have a mile and a half of surprisingly subby Strider to deal with. Sex between you and Dirk occasionally gets _really_ creative, and only Jade knows exactly how tight of a grip you have over him, thanks to that one weekend in Tokyo. It suits you both just fine, keeping it between you, and you've been toying with the idea of getting him a collar that would only come out during private visits without the others.

Maybe another day. Today, he follows you exactly half a step behind and to your left, shoulders squared and head bowed just a bit. He's not wearing his shades because you didn't say he could and he's too well trained to ask. The mall isn't too crowded yet and no one gets in your way as you lead him to a massive shoe-store, where the shoes range up even into sizes he _might_ be able to fit. Maybe. Not too many selections up that high, but size sixteen shoes are hard to come by. "See any you like?" you ask.

Dirk eyeballs the shelves warily. "You're a nine," he says slowly. "This is the wrong shelf."

"Are you telling me I'm wrong?"

"No, sir. Just that you might find better shoes an aisle over."

"If I was shopping for me, maybe." You deliberately let your voice go flat and neutral. "Are there any _you_ like? Preferably flats; you'd hit the ceiling in stilettos."

Dirk lets out a long, slow exhale. Flat tones are check points; little moments where you remind Dirk that he can back out of all of this. Deep sub-space scares him; not while he's under, but after. It's hard, keeping him in shallower waters, but you manage, mostly by jolting him out of sub-space with questions. He's beautiful when he lets everything go, but you're willing to give that up to avoid the post-scene freak-out and months of walking on eggshells.

He takes the path you hoped for, scanning the presented shoes until he finds a set of slim black flats with little bows on top. "These," he says, sitting down to try them on without prompting. _Good boy._ "Maybe I can keep some of my dignity in these."

You let him have the snarky rebellion. It puts him back into his comfort zone. He toes off his battered Converse and replaces them with the flats, then eyes them thoughtfully. "Not what I expected," he says slowly, standing to take a few test steps. He rocks up on his toes, shuffles, flash steps a few times, then nods. "These will work, sir."

"Excellent." You pay - it is your surprise, after all - and Dirk follows you out and away from the mall like an obedient puppy. He doesn't protest when you take his keys from his belt loop and let yourself into the drivers side of his car. He just gets in and rests his hands on his knees.

He's sporting a whopper of a boner.

You hum a little and slide your hand around the curve of his thigh, edging close to the tent in his pants. "I didn't think you had a shoe fetish, Dirk," you say lightly.

"I don't, sir," he says. His voice is a little wobbly. His eyes track a passing family outside of the car. "You've never taken me out like this before."

You think back. Nope, he's right, this has always been private. "Maybe I'll bring a collar and leash next time," you suggest. "So that everyone knows you're mine." Dirk's pupils contract to tiny specks and his breath hitches. You pat his leg and sit back to start the car. "But for now, we're going to get something to eat."

His muttered curse makes you smile.

O o o

It's a few hours - deliberately drawn out - before you get back to Dirk's place. "Time for your surprise," you sing, waving Dirk towards his room. "You're allowed to peek now. In fact, I want you to get dressed. Take the shoes."

"Yes, sir." Clutching at the cardboard box like a life preserver, Dirk goes into his room. You step into the guest room and you've just gotten your shirt off when you hear, very clearly, "What the fuck."

"Is there a problem?"

"Did you mix up the bags?"

"Hm." You purposefully rustle your garment bag loud enough for him to hear. "No-sirree, this is mine." You pause, just a bit. "This is the second time you've implied I'm wrong today, Dirk."

"My apologies, sir. I-"

"Just get dressed, Dirk," you sigh. "We'll correct your wayward behavior later."

Dirk doesn't respond, and you take your own advice. Off go the skirt and t-shirt and panties, all tossed carelessly onto the bed. Your suitcase yields the first part of your ensemble; a sex toy with two ends and a subtle s-curve. The shorter end slides inside you, nice and easy, with the hump of the s resting on your clit and the rest of it poking out in front of you, almost exactly where a real penis would be. You sigh and wiggle a little, testing its feel, then you fish up the next part - a rope harness.

Thank god for Roxy's knots. Thank god she showed you how to take the thingy off and on without wrecking it. The cotton rope drags against your skin as you pull it up your thighs, and you loop it into place around the dildo, right up against your mons. A little tug here, a wiggle there, and it's all in place, not going anywhere but where you decide to put it.

The rest of the outfit is easy. The toy bends enough to go into your pants without discomfort or slipping, but you still look like you're as horny as Dirk was earlier. Shirt. Jacket. Sensible shoes. No use trying to slick back your hair. A little moustache stuck to your lip and you're ready to go.

"Dirk? Are you ready?" you call out.

A long pause, long enough to wonder if he was going to call this off. "Yes, sir," he says, quiet. "I'm ready."

You straighten your shoulders and walk to Dirk's room, opening the door without knocking.

Kanaya is damn good at what she does. The dress clings tightly to Dirk's frame, hiding exactly nothing. The neckline scoops low across the pectorals and traces up around the trapezeus instead of over. The sleeves cut off halfway down the arm, defining the bicep and deltoid. The hem ends mid-thigh, showing off muscular thighs clad in slick black nylon. It is obviously a dress, and very obviously a man wearing it.

He's terribly aroused, and he's looking at you like a wary dog. 

You've spoken about doing this before, a late-night Pesterchum conversation that went personal and dark. You dont think he thought you'd ever go for it. You didn't know you would go for it, until you saw the dress Kanaya was designing for Dave and you just had to have one. "Very nice," you smile.

Dirk's eyes drop to the bulge in your slacks; a brief glance, but you notice. You tip his head up with two fingers under his chin and eye him thoughtfully. "It's very rude," you say. "Doubting me like that."

He swallows and his hands go to your waist, to your belt. "May I make it up to you, sir?" he asks, a lovely throaty sound in his voice.

You sigh. "I suppose you may." You doubt it'll be a real punishment for him, but you're curious to see what he comes up with.

Dirk's hands glide up your chest, as if you were flat, and curl around your shoulders to pull you in. His mouth is pliant and willing against yours, desperate to please, desperate for forgiveness, and you only barely respond. You do rock your hips against his thigh, pressing the toy harder against your clit, and he immediately reaches down to palm you though your slacks. You let out a pleased noise and he rubs harder, rocking the toy inside of you in tiny increments.

You pull away from his mouth and take a grip on his hair, tugging just hard enough that he knows you mean business. "You seem to want something," you say, pulling down. "And you haven't nearly made up to me yet."

"Fuck yes," he whispers, eyes blown wide as he sinks to his knees. His hands tremble a bit as he undoes your belt and your grip in his hair turns to petting as he gets your pants open. Your cock springs out, almost real enough, and he swallows again. "May I, sir?"

"Do you want me to make you beg?" Flat voice; he's sinking fast. You should have done this years ago.

His body doesn't jump, so he's not too deep yet. But he blinks a few times, then shakes his head. "Go on, then," you say. "Show me how sorry you are."

Dirk actually moans as he sinks down on your cock, the friction of his lips dragging enough to push the other end into you. He figures out what it's shaped like soon enough and uses that, his hand around the base to rock it for you even as he swallows the free end. You sigh, in pleasure this time, and reach into your pocket. "Hold out your hand," you order.

He looks up at you but does so, perfectly steady without a hand to brace on your thigh. You drizzle lube over his fingers and reach over him to hike up the back of his dress, exposing his bare butt. "Prep yourself."

He nearly chokes. You pump your hips, fucking his mouth, and his eyes fall shut. He lets go of your cock to spread his own cheeks, and you can just barely see his slick fingers prodding at his own hole.

"Perfect." He's whining under his breath in time with your thrusts, using the same rhythm with his hands. You keep it steady, petting his hair again, as he arches his back and gets his fingers as deep as he can. He holds out his hand at one point for more lube and you oblige him, careful to not spill on the carpet. 

The push-pull of the dildo builds up nice and slow, up until Dirk surges forwards to deep-throat you with a muffled groan, and you hazily wonder if he found his own prostate as your orgasm rolls over you. You shudder and he pulls back, nuzzling the side of your cock, spreading his own saliva across his cheek as he fingers himself. "More?" you ask, gripping the base of the toy and nudging his cheek.

"Please," he gasps, kissing at your fingers. You push him towards the bed and he goes willingly, on his elbows and knees with his hands in his hair and his skirt rucked up in back. You toe off your shoes and climb up behind him and slap him right across the ass as you position yourself. He jumps and cranes his neck around to glare at you and you wave back. Dirk doesn't like pain, not like Rose does, and it's as effective at bringing him back to the shallow end of the pool as any question you might ask. He huffs and settles in again, no longer quite so wanton, but he does shiver when he hears the cap to the lube pop open.

He shivers more when you press your cock into him. Just the tip at first, just enough to tease, and you hold there until he makes irritated noises and rocks back, trying to get you deeper. "Impatient," you scold, flexing your fingers around his bony hip.

"Please, sir," he says, and oh, here's a bit of begging after all. "Please fuck me."

As if you're going to say 'no' to such politeness. You pull back, just a little, then push again and you both groan. It's different than doing this with a girl; there's more friction, more resistance, and you're kind of sad that you can't feel it. But the way the toy slides inside you, and the way Dirk openly moans are good enough.

Dirk might not like pain, but he does like it harsh, and you oblige him, jerking your hips in short, hard thrusts. He swears and drops his shoulders to the bed, his knees spread wide so that you're thrusting down into him. You brace your hands on his shoulders and he nearly sobs, clutching the sheets in both fists and you don't relent, don't give him a chance to catch his breath. He pushes up against you but he can't budge you, can't get room enough to take in anything more than shallow gulps of air and it takes you a moment to realize that he's speaking on his frenzied exhales, praise and pleads in equal measure.

You shift a little more weight to your hands and his breathing cuts off and you can't move the dildo inside him anymore as he climaxes hard and clenches down around it. You sit back and move anyway, sliding it inside of you as much as you can with him and the harness holding it, and he whimpers and holds still while you finish yourself off.

You give both of you a moment before you ease out of him. Your bits are all hyper-sensitive now and you mutter a few curses as you kick out of your pants and the harness. Your jacket joins the pile on the floor, as does the toy, and you crawl up next to Dirk and hold your sub close, petting his hair while he clutches at you and remembers how to breathe.

After a few minutes, Dirk laughs breathlessly. "Kanaya is gonna kill both of us," he mutters.

You splutter a laugh. The front of your pants are splattered with lube, and the inside of his skirt is streaked with his mess. "She might," you agree. "If she doesn't suspect why I wanted all of this."

"Well, there goes my reputation," he deadpans.

You kiss his forehead. "Like you had one." You pet his hair for a moment longer, then nuzzle the top of his head. "Okay, Mr. Strider?"

He takes a moment to answer. "Yeah," he says finally. Which means he didn't fall too deep and he's not about to panic. 

"Fantastic. Welp, we should go shower and get these clothes into the wash before they stain."

"Right." He sits up, then kisses you soundly. "Thanks, Jane," he says softly, almost lovingly. You blush.

And then he flash-steps into the bathroom and locks the door, and the hot water is nearly gone by the time you get to shower.


End file.
